It is proposed to synthesize a variety of potentially therapeutically useful acyl dihydropyridines for metabolic testing as NAD antagonists. The synthesis will be extended to anhydrosugar derivatives of dihydropyridines, purines and pyrimidines. Acyl dihydropyridines will be converted to anions, radicals and cations of dihydropyridines and the chemical fates of these intermediates investigated. Nuclear magnetic resonance studies will give information on barriers to rotation and conformation. In experiments designed to observe homoconjugation in carbanions a series of pyridylalkyl organometallic compounds will be prepared and studied with chemical and nmr techniques. The role of bridged pyridyalkyl anions in rearrangement processes and in the formation of bridged pyridines will be studied. Fast rearrangements will be studied with the nmr line-shape technique. Methods are proposed for synthesizing stable acyl alkylidine dihydropyridines and investigating their chemical behavior.